高对映选择性有机催化的七元环状亚胺二苯并1,4-氧氮杂卓和丙酮的直接Mannich反应

doi:10.1016/S1872-2067(14)60225-4

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 93-99.DOI: 10.1016/S1872-2067(14)60225-4

高对映选择性有机催化的七元环状亚胺二苯并1,4-氧氮杂卓和丙酮的直接Mannich反应

汪游清, 任圆圆

河南大学天然药物与免疫工程重点实验室, 河南开封475004

收稿日期:2014-08-14 修回日期:2014-09-12 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 汪游清
基金资助:
国家自然科学基金(21002022); 教育部留学回国人员科研启动基金.

Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis

You-Qing Wang, Yuan-Yuan Ren

Provincial Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng 475004, Henan, China

Received:2014-08-14 Revised:2014-09-12 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Natural Science Foundation of China (21002022) and the Chinese Ministry of Education (the Scientific Research Foundation for the Returned Overseas Chinese Scholars).

摘要/Abstract

摘要：

用脯氨酸作为催化剂, 研究了各种取代的二苯并1,4-氧氮杂卓衍生物类七元环状亚胺和丙酮的直接Mannich反应, 该反应能高对映选择得到一系列旋光活性的含有β羰基的七元环状氮杂环化合物(93%-98% ee). 用丁酮作为Mannich给体时, 能得到专一的区域选择性和96%-97% ee的产物. 进一步通过X射线单晶衍射分析其中一个产物的衍生物, 确定了产物手性中心绝对构型为R, 其它同类型产物绝对构型随后通过化学类比方法推断确认.

关键词: 丙酮, 不对称催化, 七元环状亚胺, Mannich反应, 有机催化

Abstract:

Various substituted dibenzo[b,f][1,4]oxazepines as seven-membered cyclic imines underwent a highly enantioselective direct Mannich reaction with acetone when catalyzed by proline. These reactions gave a range of optically active β-carbonyl seven-membered N-heterocycles with excellent enantioselectivity (93%-98% ee). With 2-butanone as a Mannich donor, the single regioselective product was obtained with 96%-97% ee. The absolute configuration of the product was assigned to be R by X-ray single crystal analysis of its derivative.

Key words: Acetone, Asymmetric catalysis, Seven-membered cyclic imine, Mannich reaction, Organocatalysis

汪游清, 任圆圆. 高对映选择性有机催化的七元环状亚胺二苯并1,4-氧氮杂卓和丙酮的直接Mannich反应[J]. 催化学报, 2015, 36(1): 93-99.

You-Qing Wang, Yuan-Yuan Ren. Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis[J]. Chinese Journal of Catalysis, 2015, 36(1): 93-99.

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高对映选择性有机催化的七元环状亚胺二苯并1,4-氧氮杂卓和丙酮的直接Mannich反应

Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis

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